2,2'-[Biphenyl-2,2'-diylbis(-oxy)]diacetic acid monohydrate.

In the crystal structure of the title compound, C(16)H(14)O(6)·H(2)O, the dihedral angle between the benzene rings is 60.8 (3)°. Mol-ecules are linked through a bifurcated O-H⋯O hydrogen bond, forming a zigzag chain along the b axis. The chains are further linked by O-H⋯O hydrogen bonds mediated by water mol-ecules.

Related literature

For the crystal structures of related compounds, see: Ali, Hussain et al. (2008 ▶); Ali, Ibad et al. (2008 ▶); Ali, Shah & VanDerveer (2008 ▶); Ibad et al. (2008 ▶). For biological applications, see: Baudry et al. (2006 ▶); Kamoda et al. (2006 ▶); Litvinchuk et al. (2004 ▶); MacNeil & Decken (1999 ▶); Park (2000 ▶); Sisson et al. (2006 ▶).

Experimental

Crystal data

C16H14O6·H2O

M = 320.29

Monoclinic,

a = 13.7590 (17) Å

b = 6.7875 (9) Å

c = 16.446 (2) Å

β = 104.698 (2)°

V = 1485.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 150 (2) K

0.17 × 0.13 × 0.08 mm

Data collection

Bruker APEX 2000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.991

10352 measured reflections

2612 independent reflections

1555 reflections with I > 2σ(I)

R int = 0.078

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.088

S = 0.85

2612 reflections

216 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680802833X/is2319sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802833X/is2319Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H14O6·H2O	F(000) = 672
Mr = 320.29	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 765 reflections
a = 13.7590 (17) Å	θ = 2.6–23.3°
b = 6.7875 (9) Å	µ = 0.11 mm−1
c = 16.446 (2) Å	T = 150 K
β = 104.698 (2)°	Block, colourless
V = 1485.6 (3) Å3	0.17 × 0.13 × 0.08 mm
Z = 4

Bruker APEX 2000 CCD area-detector diffractometer	2612 independent reflections
Radiation source: fine-focus sealed tube	1555 reflections with I > 2σ(I)
graphite	Rint = 0.078
φω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→16
Tmin = 0.981, Tmax = 0.991	k = −8→8
10352 measured reflections	l = −19→19

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 0.85	w = 1/[σ2(Fo2) + (0.0212P)2] where P = (Fo2 + 2Fc2)/3
2612 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.16 e Å−3
3 restraints	Δρmin = −0.17 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O1	0.66330 (12)	0.7028 (2)	0.14229 (10)	0.0345 (5)
O2	0.77830 (14)	0.9862 (3)	0.10441 (13)	0.0575 (6)
O3	0.64570 (12)	1.1309 (3)	0.01909 (11)	0.0425 (5)
H3	0.6876	1.2187	0.0158	0.064*
O4	0.81532 (12)	0.4297 (2)	0.13157 (10)	0.0358 (5)
O5	0.74938 (13)	0.4148 (3)	−0.03373 (11)	0.0401 (5)
O6	0.88580 (13)	0.5688 (3)	−0.05041 (11)	0.0537 (6)
H6	0.8564	0.5573	−0.1016	0.080*
C1	0.60904 (18)	0.5402 (4)	0.15417 (15)	0.0291 (6)
C2	0.50827 (18)	0.5152 (4)	0.11531 (15)	0.0324 (7)
H2	0.4738	0.6084	0.0752	0.039*
C3	0.45771 (19)	0.3522 (4)	0.13553 (15)	0.0336 (7)
H3A	0.3883	0.3352	0.1094	0.040*
C4	0.50694 (18)	0.2161 (4)	0.19259 (15)	0.0354 (7)
H4	0.4724	0.1038	0.2053	0.043*
C5	0.60788 (19)	0.2438 (4)	0.23173 (15)	0.0336 (7)
H5	0.6415	0.1509	0.2725	0.040*
C6	0.66082 (18)	0.4036 (4)	0.21279 (15)	0.0281 (6)
C7	0.76791 (18)	0.4314 (3)	0.25873 (15)	0.0294 (6)
C8	0.7942 (2)	0.4382 (4)	0.34570 (17)	0.0396 (7)
H8	0.7430	0.4284	0.3749	0.048*
C9	0.8932 (2)	0.4588 (4)	0.39121 (17)	0.0445 (8)
H9	0.9096	0.4634	0.4509	0.053*
C10	0.9674 (2)	0.4726 (4)	0.34935 (18)	0.0428 (7)
H10	1.0353	0.4878	0.3803	0.051*
C11	0.94422 (19)	0.4646 (4)	0.26314 (17)	0.0383 (7)
H11	0.9962	0.4723	0.2347	0.046*
C12	0.84508 (19)	0.4451 (4)	0.21760 (16)	0.0319 (6)
C13	0.61476 (18)	0.8429 (3)	0.08196 (15)	0.0314 (6)
H13A	0.5600	0.9081	0.1009	0.038*
H13B	0.5852	0.7769	0.0276	0.038*
C14	0.6906 (2)	0.9920 (4)	0.07165 (16)	0.0326 (6)
C15	0.88486 (18)	0.4850 (4)	0.08631 (16)	0.0394 (7)
H15A	0.9416	0.3906	0.0970	0.047*
H15B	0.9119	0.6178	0.1039	0.047*
C16	0.8314 (2)	0.4852 (4)	−0.00470 (17)	0.0352 (7)
O7	0.81871 (18)	0.9230 (3)	0.28791 (13)	0.0573 (6)
H7A	0.814 (2)	1.003 (3)	0.2488 (15)	0.086*
H7B	0.795 (2)	0.818 (3)	0.2670 (18)	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0320 (11)	0.0300 (10)	0.0373 (11)	−0.0022 (9)	0.0012 (8)	0.0097 (9)
O2	0.0260 (11)	0.0528 (13)	0.0867 (17)	−0.0005 (10)	0.0012 (11)	0.0256 (12)
O3	0.0379 (12)	0.0388 (12)	0.0470 (12)	−0.0057 (9)	0.0037 (10)	0.0132 (10)
O4	0.0298 (10)	0.0457 (12)	0.0344 (11)	−0.0067 (9)	0.0127 (9)	−0.0042 (9)
O5	0.0323 (11)	0.0433 (12)	0.0435 (12)	−0.0070 (10)	0.0076 (9)	0.0037 (9)
O6	0.0405 (12)	0.0756 (15)	0.0449 (13)	−0.0172 (11)	0.0108 (10)	0.0141 (12)
C1	0.0306 (15)	0.0295 (16)	0.0297 (16)	−0.0015 (13)	0.0124 (13)	−0.0012 (13)
C2	0.0333 (16)	0.0354 (16)	0.0282 (16)	0.0033 (13)	0.0069 (13)	0.0061 (13)
C3	0.0268 (16)	0.0404 (17)	0.0340 (17)	−0.0015 (14)	0.0082 (13)	−0.0039 (14)
C4	0.0329 (17)	0.0366 (17)	0.0399 (18)	−0.0051 (14)	0.0151 (14)	−0.0011 (14)
C5	0.0333 (17)	0.0367 (17)	0.0332 (16)	0.0060 (13)	0.0128 (13)	0.0077 (13)
C6	0.0293 (15)	0.0315 (16)	0.0248 (15)	0.0030 (13)	0.0096 (12)	0.0026 (13)
C7	0.0311 (16)	0.0245 (15)	0.0312 (16)	0.0016 (12)	0.0057 (13)	0.0043 (12)
C8	0.0394 (18)	0.0409 (18)	0.0387 (18)	0.0030 (14)	0.0101 (14)	0.0079 (14)
C9	0.0443 (19)	0.0484 (19)	0.0352 (18)	0.0009 (16)	−0.0004 (15)	0.0086 (15)
C10	0.0321 (16)	0.0431 (19)	0.0453 (19)	0.0002 (15)	−0.0048 (14)	0.0042 (15)
C11	0.0277 (16)	0.0381 (17)	0.0480 (19)	0.0023 (14)	0.0079 (14)	0.0029 (14)
C12	0.0323 (16)	0.0286 (16)	0.0336 (17)	0.0022 (13)	0.0061 (13)	0.0028 (13)
C13	0.0332 (16)	0.0282 (15)	0.0306 (16)	0.0018 (13)	0.0039 (13)	0.0071 (13)
C14	0.0362 (17)	0.0300 (16)	0.0320 (17)	0.0057 (14)	0.0094 (13)	0.0074 (13)
C15	0.0295 (15)	0.0489 (19)	0.0411 (18)	−0.0045 (14)	0.0113 (14)	0.0051 (14)
C16	0.0322 (16)	0.0340 (17)	0.0416 (18)	0.0028 (14)	0.0134 (14)	0.0062 (14)
O7	0.0706 (15)	0.0440 (13)	0.0565 (15)	0.0038 (13)	0.0144 (13)	−0.0040 (11)

O1—C1	1.374 (3)	C6—C7	1.488 (3)
O1—C13	1.414 (3)	C7—C8	1.384 (3)
O2—C14	1.191 (3)	C7—C12	1.399 (3)
O3—C14	1.322 (3)	C8—C9	1.386 (3)
O3—H3	0.8400	C8—H8	0.9500
O4—C12	1.374 (3)	C9—C10	1.371 (3)
O4—C15	1.404 (3)	C9—H9	0.9500
O5—C16	1.207 (3)	C10—C11	1.373 (3)
O6—C16	1.317 (3)	C10—H10	0.9500
O6—H6	0.8400	C11—C12	1.386 (3)
C1—C2	1.382 (3)	C11—H11	0.9500
C1—C6	1.396 (3)	C13—C14	1.494 (3)
C2—C3	1.391 (3)	C13—H13A	0.9900
C2—H2	0.9500	C13—H13B	0.9900
C3—C4	1.367 (3)	C15—C16	1.491 (3)
C3—H3A	0.9500	C15—H15A	0.9900
C4—C5	1.387 (3)	C15—H15B	0.9900
C4—H4	0.9500	O7—H7A	0.833 (16)
C5—C6	1.385 (3)	O7—H7B	0.820 (16)
C5—H5	0.9500
C1—O1—C13	117.58 (19)	C8—C9—H9	120.3
C14—O3—H3	109.5	C9—C10—C11	120.6 (3)
C12—O4—C15	117.41 (19)	C9—C10—H10	119.7
C16—O6—H6	109.5	C11—C10—H10	119.7
O1—C1—C2	123.4 (2)	C10—C11—C12	120.0 (3)
O1—C1—C6	115.6 (2)	C10—C11—H11	120.0
C2—C1—C6	120.9 (2)	C12—C11—H11	120.0
C1—C2—C3	119.4 (2)	O4—C12—C11	124.0 (2)
C1—C2—H2	120.3	O4—C12—C7	115.4 (2)
C3—C2—H2	120.3	C11—C12—C7	120.6 (2)
C4—C3—C2	120.7 (2)	O1—C13—C14	108.4 (2)
C4—C3—H3A	119.7	O1—C13—H13A	110.0
C2—C3—H3A	119.7	C14—C13—H13A	110.0
C3—C4—C5	119.4 (3)	O1—C13—H13B	110.0
C3—C4—H4	120.3	C14—C13—H13B	110.0
C5—C4—H4	120.3	H13A—C13—H13B	108.4
C6—C5—C4	121.5 (2)	O2—C14—O3	124.9 (2)
C6—C5—H5	119.2	O2—C14—C13	125.7 (2)
C4—C5—H5	119.2	O3—C14—C13	109.5 (2)
C5—C6—C1	118.0 (2)	O4—C15—C16	107.7 (2)
C5—C6—C7	119.7 (2)	O4—C15—H15A	110.2
C1—C6—C7	122.2 (2)	C16—C15—H15A	110.2
C8—C7—C12	117.8 (2)	O4—C15—H15B	110.2
C8—C7—C6	119.6 (2)	C16—C15—H15B	110.2
C12—C7—C6	122.6 (2)	H15A—C15—H15B	108.5
C7—C8—C9	121.6 (3)	O5—C16—O6	123.7 (3)
C7—C8—H8	119.2	O5—C16—C15	124.8 (2)
C9—C8—H8	119.2	O6—C16—C15	111.5 (2)
C10—C9—C8	119.4 (3)	H7A—O7—H7B	107 (2)
C10—C9—H9	120.3
C13—O1—C1—C2	−5.2 (3)	C6—C7—C8—C9	178.3 (2)
C13—O1—C1—C6	178.4 (2)	C7—C8—C9—C10	−0.1 (4)
O1—C1—C2—C3	−175.6 (2)	C8—C9—C10—C11	−0.5 (4)
C6—C1—C2—C3	0.5 (4)	C9—C10—C11—C12	0.9 (4)
C1—C2—C3—C4	−0.7 (4)	C15—O4—C12—C11	−16.4 (3)
C2—C3—C4—C5	1.3 (4)	C15—O4—C12—C7	166.3 (2)
C3—C4—C5—C6	−1.7 (4)	C10—C11—C12—O4	−177.9 (2)
C4—C5—C6—C1	1.5 (4)	C10—C11—C12—C7	−0.7 (4)
C4—C5—C6—C7	177.6 (2)	C8—C7—C12—O4	177.5 (2)
O1—C1—C6—C5	175.5 (2)	C6—C7—C12—O4	−0.5 (3)
C2—C1—C6—C5	−0.9 (4)	C8—C7—C12—C11	0.1 (4)
O1—C1—C6—C7	−0.5 (3)	C6—C7—C12—C11	−177.9 (2)
C2—C1—C6—C7	−176.9 (2)	C1—O1—C13—C14	−172.89 (19)
C5—C6—C7—C8	−54.7 (3)	O1—C13—C14—O2	4.7 (4)
C1—C6—C7—C8	121.3 (3)	O1—C13—C14—O3	−176.4 (2)
C5—C6—C7—C12	123.2 (3)	C12—O4—C15—C16	−171.5 (2)
C1—C6—C7—C12	−60.8 (3)	O4—C15—C16—O5	−12.6 (4)
C12—C7—C8—C9	0.3 (4)	O4—C15—C16—O6	168.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O5i	0.84	1.87	2.671 (2)	158
O3—H3···O4i	0.84	2.66	3.285 (2)	133
O6—H6···O7ii	0.84	1.76	2.584 (3)	165
O7—H7A···O2	0.83 (2)	2.30 (2)	2.958 (3)	136 (2)
O7—H7B···O1	0.82 (2)	2.50 (2)	3.153 (3)	138 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5i	0.84	1.87	2.671 (2)	158
O3—H3⋯O4i	0.84	2.66	3.285 (2)	133
O6—H6⋯O7ii	0.84	1.76	2.584 (3)	165
O7—H7A⋯O2	0.833 (16)	2.30 (2)	2.958 (3)	136 (2)
O7—H7B⋯O1	0.820 (16)	2.50 (2)	3.153 (3)	138 (3)

Symmetry codes: (i) ; (ii) .